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KTI1VL BKNZOATE                              209

remains as an oily liquid with a fragrant smell. C(5H5COCl-f
CoHftOm- NaOll -•••Clil-lfl(:0()C,il.4-NaCl + H:iO. Repeat the
same reaction with phenol and separate the solid phenyl
ben/oat e. (Schotten-Baumann reaction.)

3. Add 5 grams benzoyl chloride to 10 grams ammonium
carbonate in a mortar* and grind up well. The reaction pro-
ceeds quietly. If after ten minutes the smell of benzoyl chloride
still remains, add a few drops of concentrated ammonia. Add
cold water and filter. Bcnxamide remains on the filter in the
form of a white crystalline powder, and maybe recrystallised
from hot water; m. p. 128'''. C(;Ilr>COCl + 2NH4HCO.} =
CCHSCON 1 1,-f N I I.tU + 2CO, + 2l!,0. See Appendix, p. 308.

Ethyl Benzoate (Ethyl  Benzoic Ester), CGH-CO.OC2H5
K. Fischer and Speier, /?<.r., 1895, 28, 1150
25 grms. benzoic acid.
75    >i      (90 c.c.) absolute alcohol.
Pass dry hydrochloric acid gas (seep. 93) through the alcohol,
cooled in water until it has increased about 3 grams in weight.
Add the benzoic acid and boil the mixture with upright con-
denser over wire-gauze for two hours. On pouring a small
quantity of the product into water, only the ester, which is a
heavy oil, should separate, but no solid benzoic acid. The
excess of alcohol is now distilled off on the water-bath and the
residue poured into water. Any free hydrochloric or benzoic
acid is removed by shaking with a dilute solution of sodium
carbonate!. On adding ether and shaking, the ester dissolves in
the top layer of ether, which is separated and dehydrated over
calcium chloride. The ether is removed on the water-bath, and
the ethyl benxoate is then distilled over wire -gauze, a few bits of
porcelain being added to prevent bumping. The distillate is
collected between 205° and 212°. Yield, about 22 grams.
C,jHr,COO M + 1 lOC.H™ C0Hf>COOC,H5 + H2O.
Properties. -Colourless, sweet-smelling oil ; b. p. 211° ; sp. gr.
1*05 at 15°.
COHKN'S ADV. p. o. c                                                   P